10931

Arachidonic acid

>95.0% (GC)

• Sinónimos: cis,cis,cis,cis-5,8,11,14-Eicosatetraenoic acid, Eicosa-5Z,8Z,11Z,14Z-tetraenoic acid, Immunocytophyte
• Fórmula lineal: CH₃(CH₂)₄(CH=CHCH₂)₄CH₂CH₂CO₂H
• Número de CAS: 506-32-1
• Peso molecular: 304.47
• Beilstein: 1713889
• Número CE: 208-033-4
• Número MDL: MFCD00004417
• Código UNSPSC: 12352211
• ID de la sustancia en PubChem: 57646859
• NACRES: NA.25

Propiedades

• origen biológico: fungus
• Análisis: >95.0% (GC)
• formulario: liquid
• índice de refracción: n20/D 1.4872 (lit.)
• bp: 169-171 °C/0.15 mmHg (lit.)
• mp: −49 °C (lit.)
• densidad: 0.922 g/mL at 25 °C (lit.)
• grupo funcional: carboxylic acid
• tipo de lípido: omega FAs
• Condiciones de envío: dry ice
• temp. de almacenamiento: −20°C
• cadena SMILES: OC(CCC/C=C\C/C=C\C/C=C\C/C=C\CCCCC)=O
• InChI: 1S/C20H32O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-,16-15-
• Clave InChI: YZXBAPSDXZZRGB-DOFZRALJSA-N

Descripción

Aplicación

Arachidonic acid has been used:

• in calibration curve generation in Raman spectroscopy and atomic force microscopy (AFM) in normal and breast cancer samples
• as a polyunsaturated fatty acid supplement to the reconstituted synthetic bile (RSB) in drug resistance analysis
• for the activation of mechanistic target of rapamycin 1 (mTOR1) and mTOR2

Acciones bioquímicas o fisiológicas

Arachidonic acid (AA) is an unsaturated ω⁶ fatty acid constituent of the phospholipids of cell membranes. Phospholipase A2 releases AA from the membrane phospholipids in response to inflammation. AA is subsequently metabolized to prostaglandins and thromboxanes by at least two cyclooxygenase (COX) isoforms, to leukotrienes and lipoxins by lipoxygenases, and to epoxyeicosatrienoic acids via cytochrome p450-catalyzed metabolism. AA and its metabolites play important roles in a variety of biological processes, including signal transduction, smooth muscle contraction, chemotaxis, cell proliferation and differentiation, and apoptosis. AA has been demonstrated to bind to the a subunit of G protein and inhibit the activity of Ras GTPase-activating proteins (GAPs). Cellular uptake of AA is energy dependent and involves protein-facilitated transport across the plasma membrane.

Arachidonic acid stimulates adhesion of MDA-MB-435 human metastatic cancer cells to extracellular matrix molecules (collagen IV and vitronectin) .

Información de seguridad

• Pictogramas: GHS07
• Palabra de señalización: Warning
• Frases de peligro: H315,H319
• Consejos de prudencia: P264 - P280 - P302 + P352 - P305 + P351 + P338 - P332 + P313 - P337 + P313
• Clasificaciones de peligro: Eye Irrit. 2 - Skin Irrit. 2
• Código de clase de almacenamiento: 10 - Combustible liquids
• Clase de riesgo para el agua (WGK): WGK 3
• Punto de inflamabilidad (°F): 235.4 °F - closed cup
• Punto de inflamabilidad (°C): 113 °C - closed cup
• Equipo de protección personal: Eyeshields, Faceshields, Gloves, multi-purpose combination respirator cartridge (US)